HCID 664093, compound → 3-(4-Benzyloxy-phenyl)-2-{4-methyl-2-[(4-phenyl-piperazine-1-carbonyl)-amino]-pentanoylamino}-propionic acid tert-butyl ester

HRID 2230301Notes

Reaction equation

HRID 2230301 reaction equation
[CH3:1][CH:2]([CH3:23])[CH2:3][C@H:4]([NH:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:5]([OH:7])=O.[C:24]([O:28][C:29](=[O:47])[C@@H:30]([NH2:46])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:34][CH:33]=1)([CH3:27])([CH3:26])[CH3:25]>>[C:24]([O:28][C:29](=[O:47])[CH:30]([NH:46][C:5](=[O:7])[CH:4]([NH:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[CH2:3][CH:2]([CH3:1])[CH3:23])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:34][CH:33]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 664093HCID 664093, compoundHCID 11151579tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoate

Product 1

HCID 700613663-(4-Benzyloxy-phenyl)-2-{4-methyl-2-[(4-phenyl-piperazine-1-carbonyl)-amino]-pentanoylamino}-propionic acid tert-butyl esterYield 46%

Procedure

A solution of the product from Example AG ((2S)-4-methyl-2-[(4-phenyl-piperazine-1-carbonyl)-amino]-pentanoic acid) (0.93 g, 2.9 mmol) and the product from Example A ((S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (1.0 g, 2.9 mmol) were coupled according to the procedure described in Example AH. The reaction mixture was purified by chromatography (silica gel, 1:1 EtOAc/heptane) to give the title compound as a white crystals (0.84 g, 46%), mp=67-69° C.

Workup

  1. customThe reaction mixture was purified by chromatography (silica gel, 1:1 EtOAc/heptane)

Sources & evidence

ORD record
ord-821d2f920899492db3fe91d348c2af84
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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